9 Ways to Wear Riding Boots ...


Knowing how to wear riding boots can be helpful wardrobe knowledge. I’d count a pair of flat riding boots as an essential and must-have for any wardrobe. Riding boots are fairly distinctive, with a typically a slim, knee-high fit. Whether you prefer a laidback look or something a bit more polished, riding boots can be worn in a variety of ways. Check out the following tips on how to stylishly wear riding boots.

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Model off Duty

Model off Duty When looking at how to wear riding boots, you can take inspiration from a lot of different fashion looks and trends. Work a model-off-duty inspired look by teaming a pair of sleek black riding boots with skinny jeans or denim shorts, a slub t-shirt, and black blazer or jacket. Keep your outfit sleek and minimalist for a truly urban, contemporary look.


Riding boots are a classic fashion staple that have been around for centuries. From traditional equestrian style to modern fashion trends, these boots are a versatile and timeless piece of footwear. Whether you’re looking for a way to dress up a casual outfit or add a touch of sophistication to a more formal look, riding boots are the perfect addition.

When it comes to styling riding boots, there are endless possibilities. You can opt for a classic equestrian look with tall boots, breeches, and a tweed jacket, or mix it up with a more contemporary style. For a model-off-duty inspired look, try pairing your boots with skinny jeans or denim shorts, a slub t-shirt, and a black blazer or jacket. This sleek and minimalist outfit will give you an urban, contemporary vibe.

Riding boots are also great for adding a touch of sophistication to a more formal look. Try pairing them with a dress or skirt, a blouse, and a tailored blazer for a chic, timeless look. Or, if you’re looking for something a bit more daring, you can try pairing them with a leather skirt, a crop top, and a statement jacket.


Equestrian Style

Equestrian Style Riding boots are named as such because, would you believe it, they’re typically worn when riding horses. Play this up by adopting an equestrian inspired look. Team your riding boots with a pair of cream fitted pants, a crisp shirt, and blazer. Tone the look down, however, with modern accessories.

Frequently asked questions

You can style riding boots in various ways, such as wearing them with skinny jeans, pairing them with a skirt or dress, or even coordinating them with leggings and a long sweater for a casual look.

Absolutely! Riding boots can look fabulous with dresses. Opt for a flowy midi dress or a casual mini dress for a chic ensemble. Just make sure the dress hem doesn't fall below the top of the boots to balance the look.

To stay on-trend in 2023, try wearing your riding boots with pieces like straight-leg jeans or a pleated skirt, and top it off with a stylish oversized blazer or a chunky knit sweater.

Riding boots are versatile and can be worn with many outfits. You can create a smart casual outfit by pairing them with jeans and a blazer, a feminine look with a floral dress, or a cozy outfit with leggings and an oversized sweater.

Yes, you can wear riding boots to work if they fit your workplace's dress code. Choose a pair in a classic color like black or brown, and pair them with tailored pants or a sophisticated dress and tights for a professional look.


Cosy Country

Cosy Country Since you’re most likely to don a pair of riding boots in the cooler months, try a creating a cosy outfit. When looking at how to wear riding boots this way, team them with plenty of knits, woollen scarves, and beanies for a weekend-in-the-country kind of look. Try a pair of riding boots in a brown or tan colour to complement the earthy, natural tones of your cosy outfit.


Riding boots are a stylish and practical choice for the cooler months. They are comfortable to wear and provide a great deal of support when walking or riding. The Cosy Country look is a great way to wear riding boots, as it combines the classic style of the boots with warm and comfortable knitwear, scarves, and beanies. Choose a pair of riding boots in a brown or tan colour to create a natural, earthy look. This look is perfect for a weekend in the country, or for any other occasion where you want to stay warm and look stylish.


Polished and Professional

Polished and Professional Make your riding boots office-friendly by working a more sophisticated look. Team your boots with a knee-length pencil skirt, silk collared shirt, blazer or trench coat for a look that is a bit more polished. However, always use your judgment as to whether the look is appropriate for your workplace.


With Skinny Jeans

With Skinny Jeans Since riding boots tend to be a slimmer fit, team them with fitted pants or skinny jeans. That way you can easily tuck them into your boots without any obvious bunching around the top of the boots. Avoid pants that are too baggy as they will exaggerate any bunching and bulk.


Riding boots are a classic style staple that can be worn in a variety of ways. They look great with skinny jeans, as the slim fit allows you to tuck them into the boots without any unsightly bunching around the top. To ensure a sleek look, avoid pairing them with overly baggy pants, as this will only draw attention to the bunching. Riding boots can also be worn with skirts, dresses, and shorts, making them an incredibly versatile and fashionable choice for any wardrobe.


With Tights

With Tights If you’re finding that most riding boots are a bit tight around the calves (I’ve been there, don’t worry), then try teaming them with stockings or tights. When looking at how to wear riding boots, steer clear of thicker, stiffer fabrics to ensure more room and a looser fit.


Pair your sleek riding boots with a chic dress and sheer tights, a look perfect for those crisp autumn days. Choosing the right texture is crucial—a finer denier tights not only add a touch of elegance but also fit comfortably into your boots without adding bulk. For a pop of color or a playful twist, opt for tights in jewel tones or with subtle patterns. Just remember, the aim is to create a streamlined silhouette that compliments your style while ensuring you stay cozy and fashionable.


Underneath Maxis

Underneath Maxis While your first instinct may often be to wear riding boots over pants or tights, why not try wearing them under maxi dresses or skirts for something a bit different? A peek of a riding boot underneath a maxi can add a little bit of edge to your look. Choose a skirt with a bit more volume, so it doesn’t cling to the boots, and wear with a cropped or biker style jacket.


With Minis

With Minis Really show off your boots, and a bit of leg, by teaming your riding boots with a cute mini skirt. Since the boots are typically a close fit to the leg, balance it out by wearing a full, pleated, or A-line mini skirt. When looking at how to style riding boots this way, choose a taller style of boot that hits at or just above the knee for a more flattering look.


Extra Detail

Extra Detail If you prefer your boots with added details, keep an eye out for those with buckles, straps, or embossed extras. The busier and bulkier the design of the boot, however, the better it is to keep the rest of your outfit fairly basic.

As mentioned previously, riding boots tend to have a slim cut. If you find that they are too tight around the calves, head to a cobbler to have them stretched (if they are leather). Do you have any tips for how to stylishly wear riding boots?

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Where Thoughts and Opinions Converge

Check target! I got a pair last fall for $35 and upgraded this year to a bit more pricey pair ($70) both from there. So cute!

do you know of any online stores that sell riding boots cheap? $30-$50 range. :)

I live for rising boots! Thanks!

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